Hydrochloric Acid → CID 86717288

HRID 588587Notes

Reaction equation

HRID 588587 reaction equation
[N:1]([O-])=O.[Na+].[C:5]1([C:11]#[C:12][C:13]2[C:14]([C:19]([F:22])([F:21])[F:20])=[N:15][NH:16][C:17]=2[NH2:18])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[ClH:23]>C(Cl)Cl>[Cl:23][C:12]1[C:11]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=2)=[N:1][N:18]=[C:17]2[NH:16][N:15]=[C:14]([C:19]([F:21])([F:22])[F:20])[C:13]=12

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 23668193Sodium NitriteHCID 1785091224-(2-phenylethynyl)-3-(trifluoromethyl)-1H-pyrazol-5-amine

Product 1

HCID 86717288CID 86717288

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-15 °C

Procedure

To a cooled (cooling bath −15° C.) stirred suspension of sodium nitrite (540 mg, 7.8 mmol) in conc. HCl (20 mL) was added a solution of 4-(2-phenylethynyl)-3-(trifluoromethyl)-1H-pyrazol-5-amine (652 mg, 2.6 mmol) in CH2Cl2 (3 mL). The cooling bath was removed and the reaction mixture was stirred at room temperature for 1 h. NaCl (900 mg) was added and the reaction heated at 50° C. for 16 h. CH2Cl2 was added to the cooled reaction mixture. The aqueous phase was extracted with CH2Cl2 twice and the organic phases combined, dried over MgSO4, filtered and evaporated. The residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:9 to 1:0) yielding the title compound as a yellow glass (115 mg) which was used in the subsequent step.

Workup

  1. temperatureTo a cooled
  2. customThe cooling bath was removed
  3. stirringthe reaction mixture was stirred at room temperature for 1 h
  4. additionNaCl (900 mg) was added
  5. temperaturethe reaction heated at 50° C. for 16 h
  6. additionCH2Cl2 was added to the cooled reaction mixture
  7. extractionThe aqueous phase was extracted with CH2Cl2 twice
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe residue was purified by column chromatography (silica gel, ethyl acetate/isohexane 1:9 to 1:0)

Sources & evidence

ORD record
ord-d87348a5f1e24d499fcd5a0aace8bcbb
Source dataset
uspto-grants-2016_01
Patent number
US09227976B2

Reaction notes

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